CA1037970A - Preparation d'un alcool m-amino-x-methylebenzyle - Google Patents

Preparation d'un alcool m-amino-x-methylebenzyle

Info

Publication number: CA1037970A
Authority: CA; Canada
Prior art keywords: xylene; nitro; mol; process according; oxygen
Prior art date: 1974-06-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA228,351A

Other languages

English (en)

Inventor

Francis C. Rauch

Anthony J. Fanelli

Gerlinde M. Blank

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-06-11

Filing date

1975-06-03

Publication date

1978-09-05

1975-06-03 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1978-09-05 Application granted granted Critical

1978-09-05 Publication of CA1037970A publication Critical patent/CA1037970A/fr

Status Expired legal-status Critical Current

Links

CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 title claims abstract description 66
238000000034 method Methods 0.000 title claims abstract description 21
229940078552 o-xylene Drugs 0.000 claims abstract description 30
FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical class CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 claims abstract description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 20
239000000203 mixture Substances 0.000 claims abstract description 17
239000001301 oxygen Substances 0.000 claims abstract description 17
229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
HFZKOYWDLDYELC-UHFFFAOYSA-N 1,2-dimethyl-4-nitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C=C1C HFZKOYWDLDYELC-UHFFFAOYSA-N 0.000 claims abstract description 12
239000007789 gas Substances 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 13
150000002730 mercury Chemical class 0.000 claims description 8
OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical compound O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 claims description 6
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 4
238000006396 nitration reaction Methods 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 abstract description 18
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract description 7
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 abstract description 3
238000000926 separation method Methods 0.000 abstract description 2
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 abstract 1
239000004009 herbicide Substances 0.000 abstract 1
230000000802 nitrating effect Effects 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
229910052753 mercury Inorganic materials 0.000 description 5
VLKYKLNZVULGQK-UHFFFAOYSA-N 1,2-dimethyl-3,4-dinitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1C VLKYKLNZVULGQK-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
-1 aliphatic monocarboxylic acid Chemical class 0.000 description 3
229940074994 mercuric sulfate Drugs 0.000 description 3
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
150000002884 o-xylenes Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000003822 preparative gas chromatography Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
BLFCXYJTVFTNRX-UHFFFAOYSA-N 2-chloro-4-(furan-2-yl)pyrimidine Chemical compound ClC1=NC=CC(C=2OC=CC=2)=N1 BLFCXYJTVFTNRX-UHFFFAOYSA-N 0.000 description 1
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
229910000497 Amalgam Inorganic materials 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA228,351A 1974-06-11 1975-06-03 Preparation d'un alcool m-amino-x-methylebenzyle Expired CA1037970A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US478190A US3929917A (en)	1974-06-11	1974-06-11	Process for the mononitration of ortho-xylene

Publications (1)

Publication Number	Publication Date
CA1037970A true CA1037970A (fr)	1978-09-05

Family

ID=23898886

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA228,351A Expired CA1037970A (fr)	1974-06-11	1975-06-03	Preparation d'un alcool m-amino-x-methylebenzyle

Country Status (3)

Country	Link
US (1)	US3929917A (fr)
BE (1)	BE830079A (fr)
CA (1)	CA1037970A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4447662A (en) *	1982-06-10	1984-05-08	Air Products And Chemicals, Inc.	Beta-dicarbonyl compounds for the promotion of aromatic nitration by nitrogen tetroxide
US4417080A (en) *	1982-06-10	1983-11-22	Air Products And Chemicals, Inc.	Solvent modification of nitrations by N2 O4 /metal acetylacetonate systems
IL106118A (en) *	1993-06-24	1997-08-14	Agan Chemical Manufacturers	Process for preparing n-alkyl-3,4-dialkyl- 2,6-dinitro- anilines and intermediates thereof
US5922913A (en) *	1998-11-06	1999-07-13	Srm Chemical, Ltd., Co.	Process for nitrating aromatic amines
DE102007010161A1 (de) *	2007-03-02	2008-09-04	Saltigo Gmbh	Verfahren zur Nitrierung substituierter Benzole in Gegenwart von Propionsäure
JP2013503185A (ja) *	2009-08-28	2013-01-31	イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー	Ｏ−キシレンおよび関連化合物のニトロ化方法

1974
- 1974-06-11 US US478190A patent/US3929917A/en not_active Expired - Lifetime
1975
- 1975-06-03 CA CA228,351A patent/CA1037970A/fr not_active Expired
- 1975-06-10 BE BE157201A patent/BE830079A/fr unknown

Also Published As

Publication number	Publication date
US3929917A (en)	1975-12-30
BE830079A (fr)	1975-12-10

Publication	Publication Date	Title
US7851649B2 (en)	2010-12-14	Process for the mononitration of alkanediols
CA1037970A (fr)	1978-09-05	Preparation d'un alcool m-amino-x-methylebenzyle
CA1038405A (fr)	1978-09-12	Procede de mononitration de l'ortho-xylene
US4952733A (en)	1990-08-28	Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloranisole
CA1307007C (fr)	1992-09-01	Procede pour la preparation du 4,6-dinitroresorcinol
US5245092A (en)	1993-09-14	Process for preparing dinitrotoluene with low by-product content
IL47244A (en)	1977-08-31	Process for the mononitration of ortho-xylene
US3423475A (en)	1969-01-21	Method for preparing 2,6-dichloro-4-nitrotoluene
US4997987A (en)	1991-03-05	Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole
Adolph	1972	Fluoronitroaliphatics. VI. Preparation of N-(2, 2, 2-fluorodinitroethyl) amides
US3910995A (en)	1975-10-07	Process for preparing 2,5-dihalo-3-nitrobenzoic acid
JP3059018B2 (ja)	2000-07-04	２，２−ビス（３−ニトロ−４−ヒドロキシフェニル）ヘキサフルオロプロパンの製造方法
EP1468983B1 (fr)	2007-11-21	Procede de production de 2,5-bis(trifluoromethyl)nitrobenzene
EP0307481A1 (fr)	1989-03-22	Procede de preparation de 3-chloro-4-fluoronitrobenzene
JPS60158118A (ja)	1985-08-19	酸無水物促進剤を用いたニトロ化反応
EP0165300B1 (fr)	1988-11-09	Nitration de l'acide phthalique et de l'anhydride phthalique en utilisant de l'acide nitrique
US4417080A (en)	1983-11-22	Solvent modification of nitrations by N2 O4 /metal acetylacetonate systems
JP3237942B2 (ja)	2001-12-10	芳香族ニトロ化合物の製造方法
US3979431A (en)	1976-09-07	Process for preparing nitroaromatic nitriles
WO1992004313A1 (fr)	1992-03-19	Procede non polluant de production d'un compose nitro aromatique sans usage d'acide mineral
EP0477853A1 (fr)	1992-04-01	Procédé et nouvel intermédiaire pour la préparation du 3,4'-diamino-diphénil-ether
JP2922590B2 (ja)	1999-07-26	４―ハロモノニトロトルエン類の製法
JPH06293709A (ja)	1994-10-21	芳香族ニトロ化合物の製造方法
KR0164447B1 (ko)	1999-03-20	방향족 화합물의 니트로화 방법
JPH0477458A (ja)	1992-03-11	２，４‐ジニトロ‐１，３，５‐トリイソプロピルベンゼンの製造方法